WO2003066583A1 - Astaxanthin esters - Google Patents

Astaxanthin esters Download PDF

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Publication number
WO2003066583A1
WO2003066583A1 PCT/EP2003/000873 EP0300873W WO03066583A1 WO 2003066583 A1 WO2003066583 A1 WO 2003066583A1 EP 0300873 W EP0300873 W EP 0300873W WO 03066583 A1 WO03066583 A1 WO 03066583A1
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WO
WIPO (PCT)
Prior art keywords
astaxanthin
feed
signifies
group
derivative
Prior art date
Application number
PCT/EP2003/000873
Other languages
English (en)
French (fr)
Inventor
Arnold Gloor
Werner Simon
Original Assignee
Dsm Ip Assets B.V.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
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Priority to AU2003205699A priority Critical patent/AU2003205699B8/en
Priority to CA2474208A priority patent/CA2474208C/en
Priority to ES03702554T priority patent/ES2297125T5/es
Priority to JP2003565958A priority patent/JP4420675B2/ja
Priority to MXPA04007557 priority patent/MX247604B/es
Application filed by Dsm Ip Assets B.V. filed Critical Dsm Ip Assets B.V.
Priority to US10/503,696 priority patent/US7253297B2/en
Priority to DE60317770T priority patent/DE60317770T3/de
Priority to EP03702554A priority patent/EP1474388B2/en
Publication of WO2003066583A1 publication Critical patent/WO2003066583A1/en
Priority to NO20043728A priority patent/NO328928B1/no
Priority to US11/652,263 priority patent/US20070110881A1/en
Priority to US11/652,264 priority patent/US20080008798A1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
    • C07C403/24—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by six-membered non-aromatic rings, e.g. beta-carotene
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/174—Vitamins
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/179—Colouring agents, e.g. pigmenting or dyeing agents
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K50/00—Feeding-stuffs specially adapted for particular animals
    • A23K50/80—Feeding-stuffs specially adapted for particular animals for aquatic animals, e.g. fish, crustaceans or molluscs
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
    • A23L5/40—Colouring or decolouring of foods
    • A23L5/42—Addition of dyes or pigments, e.g. in combination with optical brighteners
    • A23L5/43—Addition of dyes or pigments, e.g. in combination with optical brighteners using naturally occurring organic dyes or pigments, their artificial duplicates or their derivatives
    • A23L5/44—Addition of dyes or pigments, e.g. in combination with optical brighteners using naturally occurring organic dyes or pigments, their artificial duplicates or their derivatives using carotenoids or xanthophylls
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A40/00—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production
    • Y02A40/80—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production in fisheries management
    • Y02A40/81—Aquaculture, e.g. of fish
    • Y02A40/818—Alternative feeds for fish, e.g. in aquacultures

Definitions

  • Carotenoids are a group of naturally occurring organic pigments that are responsible, e.g., for the red, orange and yellow colours in the skin, flesh, shell and exoskeleton of aquatic animals.
  • astaxanthin The major carotenoid in the aquatic system is astaxanthin, and the function of astaxanthin in aquaculture (aquatic animals) is twofold. Firstly, it can be mobilized and utilized during maturation and at times of stress by certain fish species, e.g. salmonides (salmon and trout), which have evolved systems of deposition and storage of astaxanthin in their flesh; being a natural biological antioxidant, astaxanthin is more efficient than either vitamin E or beta-carotene in this regard. Secondly, astaxanthin is a natural flesh and skin colorant in aquatic animals.
  • the distinctive pink-red flesh colour of for example salmonides and many crustaceans attributed to astaxanthin plays an important role in the aesthetic attraction of the finished food product: the colour is part of the culinary appeal of for example salmonides, shrimps and also red sea bream. Astaxanthin is responsible for this coloration, and because fish and crustaceans cannot themselves synthesize astaxanthin, they rely on a dietary intake for their coloration. Under intensive culture conditions, astaxanthin is normally included in the complete feed for salmonides in order to intensify the desired flesh colour. This is essential if the farmed fish product is to mimic its wild counterpart and have maximum appeal to consumers, whose buying choice is generally influenced by the visual appearance of such products.
  • the pigmentation of the flesh is influenced by a number of exogenous and endogenous factors. Collectively these factors lead to a high variation of flesh pigmentation in any one population of a fish or crustacean species.
  • the deposition of astaxanthin in the flesh of salmonides is known to be influenced by several endogenous factors. These include the digestibility of the astaxanthin, its absorption from the intestine, its transport into the blood by lipoprotein, its metabolism and its attachment to the muscle fibre. Each factor can significantly influence the astaxanthin concentration in the flesh and the colour visualisation, and a limitation in any of these processes may result overall in insufficient flesh pigmentation.
  • astaxanthin i.e. the compound as such or a derivative thereof as a source of astaxanthin
  • the raw material matrix (feed) in which it is present influence the digestibility of the pigment and its subsequent efficacy in flesh pigmentation.
  • the digestibility of astaxanthin or a derivative thereof influences in turn the appropriate dietary inclusion rate and the regime employed for flesh pigmentation.
  • the form and the diet composition have been shown to affect the digestibility. It has been established that feeding non-formulated astaxanthin leads to almost no pigmentation effect.
  • R is in each case a group (a), (b) or (c)
  • R signifies hydrogen or the residue of a protein-forming amino acid
  • R signifies C ⁇ _ -alkyl or C 3-8 -cycloalkyl
  • R signifies C 1-12 -alkyl or C 3-8 -cycloalkyl
  • n zero or 1
  • Y signifies or C 2-7 -alkenylene
  • Z when n is zero, signifies C 3-8 -cycloalkyl, a group -CH(C 6 H 5 )OR , a group -COR 5 or a group -CH 2 N + (CH 3 ) 3 Hal " ,
  • n 1, signifies amino, a group -O-COR 6 , a group -OR 7 or a group -SR 8
  • n is zero or 1
  • n signifies alternatively aryl, heteroaryl, a group -COOR 5 or a group -CH(CH 3 )OR 4 ,
  • R signifies hydrogen or acetyl
  • R signifies hydrogen or Ci-g-alkyl
  • R signifies C 1-6 -alkyl, aryl or heteroaryl, ⁇
  • R signifies hydrogen, C ⁇ -6 -alkyl or acetyl
  • R signifies C ⁇ _ 6 -alkyl
  • HaF signifies a halogen ion.
  • any alkyl or alkenyl group containing three or more carbon atoms can be straight chain or branched.
  • Any aryl group (a significance of Z or of R in the group -O-COR signified by Z when n is 1) can be unsubstituted phenyl, naphthyl or a further multiring aromatic hydrocarbon group, or such a group featuring one or more substituents, particularly those substituents selected from C 1- -alkyl, C 1- -alkoxy, halogen and benzyloxy.
  • Halogen indicates fluorine, chlorine, bromine or iodide.
  • substituted phenyl groups are p-tolyl, 3-methoxyphenyl, 4-methoxyphenyl, 2,5-dimethoxyphenyl, 3,4-dimethoxyphenyl and 4-benzyloxyphenyl.
  • heteroaryl also a significance of Z or of R 6 in the group -O-COR 6 , means a heterocyclic group of aromatic character featuring as ring member(s) one or more heteroatoms selected from oxygen, sulphur and nitrogen.
  • heteroaryl groups are 2- or 3-furyl, 2- or 3-thienyl and 4-pyridyl.
  • the heteroaryl groups can be unsubstituted or substituted by one or more substituents as indicated hereinabove for the substituted aryl groups.
  • the group (a) and R signify -NH-CH(C 6 Hs)-COOR and phenyl ( H 5 ), and -NH-CH(CH 2 CH 2 SCH 3 )-COOR 2 and 2-mefhylfhioethyl (CH 2 CH 2 SCH 3 ) 5 respectively.
  • Other examples of the group (a) and the "residue of the protein-forming amino acid" (significance of R ) will not require specific elucidation.
  • Hal- can be a fluoride, chloride, bromide or iodide ion , preferably a chloride ion, CT
  • the astaxanthin derivatives of formula I can be in any possible isomeric form or in the form of mixtures of isomers, e.g. racemate mixtures.
  • Each of the above-named astaxanthin derivatives is preferably in the (all-E)-3,3'-rac isomeric form.
  • the six astaxanthin derivatives astaxanthin-diethyldicarbonate, -dimethyldi- succinate, -diethyldisuccinate, -dinicotinate, -dimethoxyacetate and -di-[(2-fhienyl)- acetate] are especially preferred ones in view of their stability and pigmentation properties.
  • the astaxanthin derivatives of the present invention can be manufactured in principle according to synthetic methods known per se for esterifications or amidations, according to the nature of the group R, whereby astaxanthin is reacted with the pertinent acid RCOOH as such or as its acid chloride RCOCl or acid anhydride (RCO) 2 O, or, in the cases where R signifies a group (a), with the appropriate N-carbonyl-amino acid ester of 1 2 the formula OCNCH(R )COOR .
  • RCOOH acid chloride
  • RCO acid anhydride
  • the reaction is generally conducted in an inert solvent and in the presence of an organic base.
  • the solvent which may instead act as a dispersion medium in the case of suspension rather than dissolution
  • a lower halogenated hydrocarbon e.g. methylene chloride or chloroform
  • a lower aliphatic or cyclic ether e.g. diethyl ether, or tetrahydrofuran or dioxan, respectively
  • an aromatic hydrocarbon e.g. toluene
  • a lower aliphatic ketone e.g. acetone.
  • the base is suitably a lower trialkylamine, e.g.
  • the molar ratio of astaxanthin : acid chloride or acid anhydride: base is conveniently in the range of 1 : 2 - 6 : 2 - 10.
  • the esterification is generally conducted in the temperature range of about -10°C to about +100°C, preferably of about 25°C to about 60°C, and most preferably of about 25°C to about 40°C. Under such conditions the esterification is generally complete within about 1 to 24 hours, usually within about 2 to 6 hours, from the start of the reaction.
  • the conditions are generally similar to those employed for esterifications with an acid chloride or anhydride in respect of the solvent/ dispersion medium and reaction temperatures.
  • a dehydrating agent is generally employed instead of a base.
  • a particularly suitable dehydrating agent is dicyclohexylcarbodiimide.
  • the molar ratio of astaxanthin : carboxylic acid : dehydrating agent is conveniently in the range of 1 : 2 - 6 : 2 - 7. Esterifications using the appropriate carboxylic acid are generally complete within a few minutes up to about 18 hours.
  • boron trifluoride etherate or a tin or zinc salt, such as the respective chloride is conveniently 1 : 2 - 4, preferably 1 : 2.2 - 2.4.
  • abase particularly triethylamine or 4-dimethylaminopyridine
  • the amount of such basic catalyst relative to the amount of astaxanthin starting material, expressed in equivalents (based on 1 equivalent of astaxanthin) is generally in the range of about 0.5 to about 10.0 (triethylamine) or of about 0.1 to about 10.0 (4-dimethylaminopyridine).
  • the amount of said Lewis acid relative to the amount of astaxanthin (1 equivalent) is generally in the range of about 0.05 to about 0.5, preferably in the range of about 0.1 to about 0.2 equivalents. Under such conditions the reaction in this case is generally complete after a much longer period, usually up to 72 hours. However, using zinc dichloride as the Lewis acid, for example, the reaction is generally complete in as short a period as from about 1 to about 3 hours.
  • the product i.e. the astaxanthin derivative of formula I
  • the product can be isolated and purified by methods known per se, e.g. by adding a solvent such as methanol to induce the separation of the crude product from the mixture after reaction, and crystallization of the collected crude product.
  • the astaxanthin derivatives of the present invention are useful as pigments in aquaculture, especially for the feed of aquatic animals, and accordingly are useful as the or a pigmenting agent in such feed.
  • Aquatic animals within the meaning of the present invention are fish, particularly marine, freshwater, anadromous or catadromous finfish, and Crustacea species.
  • Preferred fish for which the aforementioned feed for aquatic animals is very applicable are red sea bream, yellowtail, trout, salmon, tilapia, catfish and goldfish, Atlantic and Pacific salmon and trout being especially preferred.
  • Preferred crustaceans are prawns, shrimps and crayfish.
  • the astaxanthin derivatives may be incorporated in the feed by methods known per se in the art of feed formulation and processing, in principle by admixture with at least some of the components of the final feed at an appropriate stage of its manufacture.
  • the astaxanthin esters are normally incorporated as a formulation, particularly a water- dispersible formulation.
  • Such a formulation can be produced in principle by first dissolving the astaxanthin derivative in a plant or vegetable oil or fat, e.g. corn oil, or in an organic solvent, e.g.
  • the dissolution can be effected in a broad temperature range, e.g. in the range from room temperature to about 150°C. In the case of using methylene chloride as the organic solvent for the dissolution, this can be effected at room temperature or at temperatures up to about 30°C, or at higher temperatures on application of elevated pressure.
  • methylene chloride in particular dissolves the astaxanthin derivatives so readily that further economic savings are gained through the use of relatively low volumes of this solvent; as one result thereof, less of the solvent needs to be removed by evaporation and then disposed of or recycled, and as another, the processing of the lower solution volume can be effected more rapidly.
  • the solution is normally emulsified with an aqueous solution of a protective colloid, e.g.
  • a plant or animal protein such as a gelatin, particularly fish gelatin; a carbohydrate; polysaccharide; or a ligninsulphonate.
  • the solvent and water are then at least partially removed, thus affording the formulation as a concentrated emulsion.
  • the concentrated emulsion can either be directly spray-dried by conventional spray-drying techniques or spray-dried into fluidized starch or an alternative carrier, e.g. calcium silicate, again by conventional techniques.
  • the product of such spray-drying consists of beadlets, which, apart from the astaxanthin derivative itself contain components from the previous processing, e.g.
  • the beadlets may contain relatively minor amounts of stabilizers, emulsifying agents and other conventional formulation aids.
  • the preparation is conventionally then mixed with other components of the feed, such as fish oil and fish meal, and the mixture is subjected to a hydrothermal process, e.g.
  • pelleting or extrusion with application of high shear, to produce the feed for aquatic animals, supplemented with the astaxanthin derivative, in pelleted form.
  • temperatures in the range of about 70 to about 150°C, especially about 90 to about 130°C, and pressures in the range of about 10 to about 100 bar, especially about 20 to about 40 bar, may be reached.
  • the incorporated pigment in this case the astaxanthin derivative of the formula I, is able to sustain such high temperatures and pressures without excessive degradation.
  • the content of this pigmenting agent in a so-manufactured fish feed is generally in the range of about 30 to about 100 ppm.
  • the formulation for incorporation may be diluted in water and then added to and admixed with the feed for aquatic animals after said feed has been subjected to the hydrothermal process.
  • compositions containing astaxanthin derivatives of the present invention for incorporation into feed for aquatic animals, and such feed containing an effective amount of the astaxanthin derivative as a pigmenting agent, particularly a feed for aquatic animals containing from about 30 to about 100 ppm of such an astaxanthin derivative.
  • the crystals were diluted with 291 g of methylene chloride, and the solution was added to a 7.9 molar aqueous solution of sulphuric acid already warmed to 27°C. After stirring for 1.5 hours 350 ml of water were added, and the organic phase was separated. The organic phase was washed with two 200 ml portions water. The aqueous phases were washed with 200 ml of methylene chloride, and the organic phases were combined. The combined organic phase was then dried with 104.8 g of anhydrous sodium sulphate, filtered and evaporated to dryness. The resulting crystals were diluted in 228 g of toluene at room temperature.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Zoology (AREA)
  • Animal Husbandry (AREA)
  • Insects & Arthropods (AREA)
  • Nutrition Science (AREA)
  • Marine Sciences & Fisheries (AREA)
  • Birds (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Fodder In General (AREA)
  • Feed For Specific Animals (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Furan Compounds (AREA)
  • Pyridine Compounds (AREA)
PCT/EP2003/000873 2002-02-06 2003-01-29 Astaxanthin esters WO2003066583A1 (en)

Priority Applications (11)

Application Number Priority Date Filing Date Title
EP03702554A EP1474388B2 (en) 2002-02-06 2003-01-29 Astaxanthin esters
CA2474208A CA2474208C (en) 2002-02-06 2003-01-29 Astaxanthin esters
ES03702554T ES2297125T5 (es) 2002-02-06 2003-01-29 Ésteres de astaxantina
JP2003565958A JP4420675B2 (ja) 2002-02-06 2003-01-29 アスタキサンチンエステル
MXPA04007557 MX247604B (es) 2002-02-06 2003-01-29 Esteres de astaxantina.
AU2003205699A AU2003205699B8 (en) 2002-02-06 2003-01-29 Astaxanthin esters
US10/503,696 US7253297B2 (en) 2002-02-06 2003-01-29 Astaxanthin esters
DE60317770T DE60317770T3 (de) 2002-02-06 2003-01-29 Astaxanthinester
NO20043728A NO328928B1 (no) 2002-02-06 2004-09-06 Astaksantinestere
US11/652,263 US20070110881A1 (en) 2002-02-06 2007-01-10 Astaxanthin esters
US11/652,264 US20080008798A1 (en) 2002-02-06 2007-01-10 Salts of astaxathin esters

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP02002728 2002-02-06
EP02002728.0 2002-02-06

Related Child Applications (2)

Application Number Title Priority Date Filing Date
US11/652,263 Division US20070110881A1 (en) 2002-02-06 2007-01-10 Astaxanthin esters
US11/652,264 Continuation-In-Part US20080008798A1 (en) 2002-02-06 2007-01-10 Salts of astaxathin esters

Publications (1)

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WO2003066583A1 true WO2003066583A1 (en) 2003-08-14

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Country Status (13)

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US (2) US7253297B2 (enrdf_load_stackoverflow)
EP (1) EP1474388B2 (enrdf_load_stackoverflow)
JP (1) JP4420675B2 (enrdf_load_stackoverflow)
KR (1) KR100958483B1 (enrdf_load_stackoverflow)
CN (1) CN100375740C (enrdf_load_stackoverflow)
AU (1) AU2003205699B8 (enrdf_load_stackoverflow)
CA (1) CA2474208C (enrdf_load_stackoverflow)
DE (1) DE60317770T3 (enrdf_load_stackoverflow)
ES (1) ES2297125T5 (enrdf_load_stackoverflow)
IN (1) IN2004CH01714A (enrdf_load_stackoverflow)
MX (1) MX247604B (enrdf_load_stackoverflow)
NO (1) NO328928B1 (enrdf_load_stackoverflow)
WO (1) WO2003066583A1 (enrdf_load_stackoverflow)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004011423A3 (en) * 2002-07-29 2004-05-06 Hawaii Biotech Inc Structural carotenoid analogs for the inhibition and amelioration of disease
EP1563081A4 (en) * 2002-10-25 2005-10-26 PROCESS FOR PRODUCING ESTERIFIED ASTAXANTHIN FROM ESTERIFIED ZEAXANTHINE
WO2005102356A1 (en) * 2004-04-14 2005-11-03 Hawaii Biotech, Inc. Carotenoid analogs or derivatives for the inhibition and amelioration of inflammation
WO2006041903A2 (en) 2004-10-08 2006-04-20 Coho Hydroclean Sa A method of cultivating animals to develop a desired color and to increase their rate of growth
US7247752B2 (en) 2004-10-01 2007-07-24 Cardax Pharmaceuticals, Inc. Methods for the synthesis of astaxanthin
EP1867327A1 (en) 2006-06-16 2007-12-19 Yamaha Hatsudoki Kabushiki Kaisha Astaxanthin and esters thereof for protecting neurocytes and treating Parkinson's disease
US7320997B2 (en) 2002-07-29 2008-01-22 Cardax Pharmaceuticals, Inc. Pharmaceutical compositions including carotenoid ester analogs or derivatives for the inhibition and amelioration of disease
US7345091B2 (en) 2002-07-29 2008-03-18 Cardax Pharmaceuticals, Inc. Carotenoid ether analogs or derivatives for the inhibition and amelioration of disease
US7375133B2 (en) 2002-07-29 2008-05-20 Cardax Pharmaceuticals, Inc. Pharmaceutical compositions including carotenoid ether analogs or derivatives for the inhibition and amelioration of disease
EP1952845A1 (en) 2007-01-26 2008-08-06 DSMIP Assets B.V. Use of an astaxathin derivative for cosmetic purposes
US7521584B2 (en) 2002-07-29 2009-04-21 Cardax Pharmaceuticals, Inc. Carotenoid analogs or derivatives for the inhibition and amelioration of disease
WO2009027499A3 (de) * 2007-08-31 2009-05-07 Basf Se Verfahren zur herstellung von öligen lösungen von astaxanthin-derivaten
WO2009112506A1 (en) * 2008-03-11 2009-09-17 Dsm Ip Assets B.V. Novel use of carotenoid (ester)s
WO2010062189A1 (en) * 2008-11-28 2010-06-03 Pronova Biopharma Norge As A composition, with/without at least one easily oxidised component, comprising an edible processed oil or fat mixture, for promoting growth in an animal, preventing oxidative stress, avoiding that fish develop enlarged live and feed composition
WO2010100229A1 (de) * 2009-03-05 2010-09-10 Basf Se Pulverförmige zusammensetzungen von astaxanthin-derivaten ii
WO2010100233A1 (de) 2009-03-05 2010-09-10 Basf Se Verfahren zur herstellung von lösungen von astaxanthin-derivaten
WO2010100227A1 (de) 2009-03-05 2010-09-10 Basf Se Formulierung von astaxanthin-derivaten und deren verwendung ii
WO2010100228A1 (de) 2009-03-05 2010-09-10 Basf Se Pulverförmige zusammensetzung von astaxanthin-derivaten i
WO2010100226A1 (de) 2009-03-05 2010-09-10 Basf Se Formulierung von astaxanthin-derivaten und deren verwendung i
WO2010100232A3 (de) * 2009-03-05 2011-01-27 Basf Se Formulierung von astaxanthin-derivaten und deren verwendung iii
WO2011095571A2 (de) 2010-02-08 2011-08-11 Basf Se Verfahren zur herstellung von astaxanthin-dimethyldisuccinat
US8211461B2 (en) 2004-09-28 2012-07-03 Chemaphor Inc. Compositions and methods for promoting weight gain and feed conversion
US8492579B2 (en) 2010-02-08 2013-07-23 Basf Se Method for producing astaxanthin dimethyldisuccinate
US8809398B2 (en) 2007-01-16 2014-08-19 Basf Se Liquid formulations containing a carotinoid
US9180111B2 (en) 2005-03-29 2015-11-10 Cardax Pharma, Inc. Reduction in complement activation and inflammation during tissue injury by carotenoids, carotenoid analogs, or derivatives thereof
WO2016037785A1 (de) 2014-09-11 2016-03-17 Basf Se Verfahren zur herstellung von astaxanthinestern
WO2016063278A1 (en) * 2014-10-19 2016-04-28 Shenkar College Of Engineering And Design Astaxanthin based polymer and uses thereof
US9375387B2 (en) 2008-10-07 2016-06-28 Basf Se Ready-to-use, stable emulsion
KR20170007304A (ko) 2014-05-20 2017-01-18 후지카가쿠고교가부시키가이샤 카로테노이드 유도체, 그 약학상 허용되는 염 또는 그 약학상 허용되는 에스테르류 혹은 아미드류
US10449247B2 (en) 2007-10-26 2019-10-22 Avivagen Inc. Compositions and methods for enhancing immune response
US10456369B2 (en) 2009-04-30 2019-10-29 Avivagen Inc. Methods and compositions for improving the health of animals
US11185093B2 (en) 2007-11-29 2021-11-30 Christian Köpsel Pulverulent carotenoid preparation for colouring drinks
EP4067342A1 (en) 2021-04-02 2022-10-05 Kemijski Institut Sustainable preparation of xanthophyll esters

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US20080008798A1 (en) * 2002-02-06 2008-01-10 Arnold Gloor Salts of astaxathin esters
CN103589650A (zh) 2005-03-18 2014-02-19 米克罗比亚公司 产油酵母和真菌中类胡萝卜素的产生
KR20090017502A (ko) * 2006-04-05 2009-02-18 체마폴, 인코포레이티드. 식료품 보충제 및 그의 용도
US8691555B2 (en) 2006-09-28 2014-04-08 Dsm Ip Assests B.V. Production of carotenoids in oleaginous yeast and fungi
GB201009271D0 (en) 2010-06-02 2010-07-21 Promar As Compositions
EP3030648B1 (en) 2013-08-08 2020-01-08 Knipbio, Inc. Methylotrophs for aquaculture and animal feed
CN106543323B (zh) * 2015-09-23 2018-10-16 合肥炜烨光学科技有限公司 一种聚类胡萝卜素丙烯酸酯蓝光吸收剂及其制备方法
CN105504865A (zh) * 2015-12-15 2016-04-20 重庆大学 一种酯化修饰萝卜红色素的制备及纯化方法
CN105646869B (zh) * 2016-01-04 2018-01-16 中国海洋大学 一种水溶性虾青素衍生物及其制备方法
WO2018050792A1 (en) * 2016-09-16 2018-03-22 Basf Se Process for preparing esters of 12'-apocarotenals as building blocks for carotenoids
CN106748946A (zh) * 2017-02-14 2017-05-31 烟台固特丽生物科技股份有限公司 一种含水溶性虾青素作物营养液的制备方法
JP2022549503A (ja) * 2019-09-27 2022-11-25 カーダックス、インコーポレイティッド アスタキサンチンエステルおよびその使用方法
CN118063368B (zh) * 2024-04-22 2024-08-02 潍坊富邦药业有限公司 一种水溶性虾青素衍生物及其合成方法
CN118084755B (zh) * 2024-04-22 2024-08-02 潍坊富邦药业有限公司 一种高水溶性虾青素衍生物及制备方法
CN118108646B (zh) * 2024-04-22 2024-08-02 潍坊富邦药业有限公司 一种水溶性虾青素衍生物及其制备方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000062625A1 (en) 1999-04-19 2000-10-26 Norsk Hydro Asa Pigment

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4871551A (en) 1988-02-08 1989-10-03 Microbio Resources, Inc. Pigmentation supplements for animal feed compositions
JPH01202261A (ja) 1988-02-09 1989-08-15 Kyowa Hakko Kogyo Co Ltd 赤色魚用餌料と赤色魚の養殖方法
DE4322277A1 (de) * 1993-07-05 1995-01-12 Basf Ag Verbessertes Verfahren zur Herstellung von Astaxanthin, neue Zwischenprodukte hierfür sowie ein Verfahren zu deren Herstellung
DE4430289A1 (de) * 1993-09-04 1995-03-09 Basf Ag Verbessertes Verfahren zur Herstellung von Astaxanthin
JPH07300421A (ja) † 1994-04-28 1995-11-14 Itano Reitou Kk 抗炎症剤
DE19649062A1 (de) 1996-11-27 1998-05-28 Basf Ag Flüssige, mit Öl mischbare Carotinoid-Zubereitungen
US5959138A (en) † 1997-11-25 1999-09-28 Industrial Organica S.A. De C.V. Short chain diesters and process for making the same
CA2261456A1 (en) † 1998-02-23 1999-08-23 F. Hoffmann-La Roche Ag Preparation of a finely divided pulverous carotenoid preparation
NL1010351C2 (nl) † 1998-10-19 2001-01-08 Werklust & Beheer B V Esters van caroteno´den voor gebruik in de preventie en behandeling van oogaandoeningen.

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000062625A1 (en) 1999-04-19 2000-10-26 Norsk Hydro Asa Pigment

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
ANDERSSON ET AL., J.CHEM.SOC., vol. 15, 2000, pages 2409 - 2414
ANDERSSON, THOMAS ET AL: "Absolute configurational assignment of 3-hydroxycarotenoids", PERKIN 1 (2000), (15), 2409-2414, XP002239686 *
FEED MANUFACTURING TECHNOLOGY IV, 1994, pages 509 - 515

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2392562A1 (en) * 2002-07-29 2011-12-07 Cardax Pharmaceuticals, Inc. Structural carotenoid analogs for the inhibition and amelioration of disease
US7317008B2 (en) 2002-07-29 2008-01-08 Cardax Pharmaceuticals, Inc. Carotenoid ester analogs or derivatives for the inhibition and amelioration of ischemic reperfusion injury
US7592449B2 (en) 2002-07-29 2009-09-22 Cardax Pharmaceuticals, Inc. Structural carotenoid analogs for the inhibition and amelioration of disease
WO2004011423A3 (en) * 2002-07-29 2004-05-06 Hawaii Biotech Inc Structural carotenoid analogs for the inhibition and amelioration of disease
US7145025B2 (en) 2002-07-29 2006-12-05 Hawaii Biotech, Inc. Structural carotenoid analogs for the inhibition and amelioration of disease
US7521584B2 (en) 2002-07-29 2009-04-21 Cardax Pharmaceuticals, Inc. Carotenoid analogs or derivatives for the inhibition and amelioration of disease
US7345091B2 (en) 2002-07-29 2008-03-18 Cardax Pharmaceuticals, Inc. Carotenoid ether analogs or derivatives for the inhibition and amelioration of disease
US7375133B2 (en) 2002-07-29 2008-05-20 Cardax Pharmaceuticals, Inc. Pharmaceutical compositions including carotenoid ether analogs or derivatives for the inhibition and amelioration of disease
US7320997B2 (en) 2002-07-29 2008-01-22 Cardax Pharmaceuticals, Inc. Pharmaceutical compositions including carotenoid ester analogs or derivatives for the inhibition and amelioration of disease
EP1563081A4 (en) * 2002-10-25 2005-10-26 PROCESS FOR PRODUCING ESTERIFIED ASTAXANTHIN FROM ESTERIFIED ZEAXANTHINE
US7291749B2 (en) 2002-10-25 2007-11-06 Dsm Ip Assets B.V. Method for producing esterified astaxanthin from esterified zeaxanthin
WO2005102356A1 (en) * 2004-04-14 2005-11-03 Hawaii Biotech, Inc. Carotenoid analogs or derivatives for the inhibition and amelioration of inflammation
US7691901B2 (en) 2004-04-14 2010-04-06 Cardax Pharmaceuticals Inc. Carotenoid analogs or derivatives for the inhibition and amelioration of inflammation
US8211461B2 (en) 2004-09-28 2012-07-03 Chemaphor Inc. Compositions and methods for promoting weight gain and feed conversion
US7247752B2 (en) 2004-10-01 2007-07-24 Cardax Pharmaceuticals, Inc. Methods for the synthesis of astaxanthin
WO2006041903A2 (en) 2004-10-08 2006-04-20 Coho Hydroclean Sa A method of cultivating animals to develop a desired color and to increase their rate of growth
US9180111B2 (en) 2005-03-29 2015-11-10 Cardax Pharma, Inc. Reduction in complement activation and inflammation during tissue injury by carotenoids, carotenoid analogs, or derivatives thereof
EP1867327A1 (en) 2006-06-16 2007-12-19 Yamaha Hatsudoki Kabushiki Kaisha Astaxanthin and esters thereof for protecting neurocytes and treating Parkinson's disease
US8809398B2 (en) 2007-01-16 2014-08-19 Basf Se Liquid formulations containing a carotinoid
EP1952845A1 (en) 2007-01-26 2008-08-06 DSMIP Assets B.V. Use of an astaxathin derivative for cosmetic purposes
WO2009027499A3 (de) * 2007-08-31 2009-05-07 Basf Se Verfahren zur herstellung von öligen lösungen von astaxanthin-derivaten
US10449247B2 (en) 2007-10-26 2019-10-22 Avivagen Inc. Compositions and methods for enhancing immune response
US11185093B2 (en) 2007-11-29 2021-11-30 Christian Köpsel Pulverulent carotenoid preparation for colouring drinks
US8709110B2 (en) 2008-03-11 2014-04-29 Dsm Ip Assets B.V. Use of carotenoid (ester)s
WO2009112506A1 (en) * 2008-03-11 2009-09-17 Dsm Ip Assets B.V. Novel use of carotenoid (ester)s
US10004670B2 (en) 2008-10-07 2018-06-26 Basf Se Ready-to-use, stable emulsion
US9375387B2 (en) 2008-10-07 2016-06-28 Basf Se Ready-to-use, stable emulsion
WO2010062189A1 (en) * 2008-11-28 2010-06-03 Pronova Biopharma Norge As A composition, with/without at least one easily oxidised component, comprising an edible processed oil or fat mixture, for promoting growth in an animal, preventing oxidative stress, avoiding that fish develop enlarged live and feed composition
WO2010100228A1 (de) 2009-03-05 2010-09-10 Basf Se Pulverförmige zusammensetzung von astaxanthin-derivaten i
WO2010100226A1 (de) 2009-03-05 2010-09-10 Basf Se Formulierung von astaxanthin-derivaten und deren verwendung i
WO2010100229A1 (de) * 2009-03-05 2010-09-10 Basf Se Pulverförmige zusammensetzungen von astaxanthin-derivaten ii
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US10456369B2 (en) 2009-04-30 2019-10-29 Avivagen Inc. Methods and compositions for improving the health of animals
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EP1474388B1 (en) 2007-11-28
KR20040083437A (ko) 2004-10-01
AU2003205699B8 (en) 2008-06-05
US20070110881A1 (en) 2007-05-17
IN2004CH01714A (enrdf_load_stackoverflow) 2006-02-24
US20050096477A1 (en) 2005-05-05
JP4420675B2 (ja) 2010-02-24
MX247604B (es) 2007-07-30
CN1628097A (zh) 2005-06-15
DE60317770T2 (de) 2008-10-30
EP1474388A1 (en) 2004-11-10
CA2474208A1 (en) 2003-08-14
NO328928B1 (no) 2010-06-21
MXPA04007557A (es) 2004-11-10
ES2297125T3 (es) 2008-05-01
DE60317770D1 (en) 2008-01-10
JP2005517010A (ja) 2005-06-09
NO20043728D0 (no) 2004-09-06
KR100958483B1 (ko) 2010-05-17
ES2297125T5 (es) 2013-07-03
CN100375740C (zh) 2008-03-19
CA2474208C (en) 2011-03-29
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